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EP3536685B1 - Bicyclic-fused heteroaryl or aryl compounds and their use as irak4 inhibitors - Google Patents

Bicyclic-fused heteroaryl or aryl compounds and their use as irak4 inhibitors Download PDF

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Publication number
EP3536685B1
EP3536685B1 EP19157789.9A EP19157789A EP3536685B1 EP 3536685 B1 EP3536685 B1 EP 3536685B1 EP 19157789 A EP19157789 A EP 19157789A EP 3536685 B1 EP3536685 B1 EP 3536685B1
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EP
European Patent Office
Prior art keywords
compound
methoxy
carboxamide
oxopyrrolidin
fluoro
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
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EP19157789.9A
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German (de)
English (en)
French (fr)
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EP3536685A1 (en
Inventor
David Randolph ANDERSON
Mark Edward Bunnage
Kevin Joseph Curran
Christoph Martin Dehnhardt
Lori Krim Gavrin
Joel Adam Goldberg
Seungil Han
David Hepworth
Horng-Chih Huang
Arthur Lee
Katherine Lin Lee
Frank Eldridge Lovering
Michael Dennis Lowe
John Paul Mathias
Nikolaos PAPAIOANNOU
Akshay PATNY
Betsy Susan PIERCE
Eddine Saiah
Joseph Walter Strohbach
John David TRZUPEK
Richard Vargas
Xiaolun Wang
Stephen Wayne Wright
Christoph Wolfgang ZAPF
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Pfizer Inc
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Pfizer Inc
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Priority to PL19157789T priority Critical patent/PL3536685T3/pl
Priority to SI201531825T priority patent/SI3536685T1/sl
Priority to RS20220257A priority patent/RS63024B1/sr
Priority to HRP20220362TT priority patent/HRP20220362T1/hr
Publication of EP3536685A1 publication Critical patent/EP3536685A1/en
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Publication of EP3536685B1 publication Critical patent/EP3536685B1/en
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Definitions

  • Stereoisomers of Formula III include cis and trans isomers, optical isomers such as R and S enantiomers, diastereomers, geometric isomers, rotational isomers, conformational isomers, and tautomers of the compounds of the invention, including compounds exhibiting more than one type of isomerism; and mixtures thereof (such as racemates and diastereomeric pairs). Also included are acid addition or base addition salts wherein the counterion is optically active, for example, D-lactate or L-lysine, or racemic, for example, DL-tartrate or DL-arginine.
  • GI disorders include, but are not limited to: Irritable Bowel Syndrome (IBS), Inflammatory Bowel Disease (IBD), biliary colic and other biliary disorders, renal colic, diarrhea-dominant IBS, pain associated with GI distension, ulcerative colitis, Crohn's Disease, irritable bowel syndrome, Celiac disease, proctitis, eosinophilic gastroenteritis, mastocytosis, or an indication listed in a separate disease category herein.
  • IBS Irritable Bowel Syndrome
  • IBD Inflammatory Bowel Disease
  • biliary colic and other biliary disorders renal colic
  • diarrhea-dominant IBS pain associated with GI distension
  • ulcerative colitis Crohn's Disease
  • irritable bowel syndrome Celiac disease
  • proctitis proctitis
  • eosinophilic gastroenteritis eosinophilic gastroenteritis
  • mastocytosis or an indication listed in a separate
  • Specific allergic diseases include, but are not limited to: anaphylaxis, allergic rhinitis, allergic dermatitis, allergic urticaria, angioedema, allergic asthma, allergic reactions to: food, drugs, insect bites, pollen; or an indication listed in a separate disease category herein.
  • Specific skin/ dermatological diseases include, but are not limited to: psoriasis, atopic dermatitis, cutaneous lupus, acne, dermatomyositis, eczema, pruritus, scleroderma, Sweet Syndrome/neutrophilic dermatosis, neutrophilic panniculitis, acrodermatitis (form of pustular psoriasis), or an indication listed in a separate disease category herein.
  • Suitable subjects according to the present invention include mammalian subjects. Mammals according to the present invention include, but are not limited to, canine, feline, bovine, caprine, equine, ovine, porcine, rodents, lagomorphs, primates, and the like, and encompass mammals in utero. In one embodiment, humans are suitable subjects. Human subjects may be of either gender and at any stage of development.
  • Typical formulations for this purpose include gels, hydrogels, lotions, solutions, creams, ointments, dusting powders, dressings, foams, films, skin patches, wafers, implants, sponges, fibers, bandages and microemulsions. Liposomes may also be used.
  • Typical carriers include alcohol, water, mineral oil, liquid petrolatum, white petrolatum, glycerin, polyethylene glycol and propylene glycol.
  • Penetration enhancers may be incorporated; see, for example, J. Pharm. Sci., 88(10), 955-958, by Finnin and Morgan (October 1999 ).
  • the present invention includes the use of a combination of an IRAK inhibitor compound as provided in the compound of Formula III and one or more additional pharmaceutically active agent(s). If a combination of active agents is administered, then they may be administered sequentially or simultaneously, in separate dosage forms or combined in a single dosage form. Accordingly, the present invention also includes pharmaceutical compositions comprising an amount of: (a) a first agent comprising a compound of Formula III or a pharmaceutically acceptable salt of the compound; (b) a second pharmaceutically active agent; and (c) a pharmaceutically acceptable carrier, vehicle or diluent.
  • TWEAK receptor TNF superfamily receptor 12A
  • BIIB-023, enavatuzumab, and RG-7212 TNF superfamily receptor 12A
  • Inhibitors of xanthine oxidase including but not limited to, allopurinol, benzbromarone, febuxostat, topiroxostat, tisopurine and inositols;
  • Inhibitors of URAT1 include but not limited to, lesinurad, RDEA 3170, UR1102 and levotofispam;
  • Inhibitors of thymic stromal lymphoprotein including but not limited to, AMG157;
  • Agents for treating diabetic nephropathy including but not limited to, DA-9801 and ASP-8232;
  • Such inhibitors include, but are not limited to, boroarginine derivatives, boropeptides, heparins, hirudin, argatroban, and melagatran, including pharmaceutically acceptable salts and prodrugs thereof.
  • Boroarginine derivatives and boropeptides include N-acetyl and peptide derivatives of boronic acid, such as C-terminal alpha-aminoboronic acid derivatives of lysine, ornithine, arginine, homoarginine and corresponding isothiouronium analogs thereof.
  • hirudin includes suitable derivatives or analogs of hirudin, referred to herein as hirulogs, such as disulfatohirudin.
  • anistreplase refers to anisoylated plasminogen streptokinase activator complex, as described, for example, in EP 028,489, the disclosure of which is hereby incorporated herein by reference herein.
  • urokinase as used herein, is intended to denote both dual and single chain urokinase, the latter also being referred to herein as prourokinase.
  • TGR5 also termed GPBAR1 receptor modulators, particularly agonists, such as those described in Zhong, M., Current Topics in Medicinal Chemistry, 2010, 10(4), 386-396 and INT777, GPR40 agonists, such as those described in Medina, J.C., Annual Reports in Medicinal Chemistry, 2008, 43, 75-85 , including but not limited to TAK-875, GPR120 modulators, particularly agonists, high affinity nicotinic acid receptor (HM74A) activators, and SGLT1 inhibitors, such as GSK1614235.
  • HM74A high affinity nicotinic acid receptor
  • anti-diabetic agents that can be combined with the compounds of the present invention can be found, for example, at page 28, line 35 through page 30, line 19 of WO2011005611 .
  • Preferred anti-diabetic agents are metformin and DPP-IV inhibitors (e.g., sitagliptin, vildagliptin, alogliptin, dutogliptin, linagliptin and saxagliptin).
  • the reaction mixture was cooled to about 25 °C, diluted with EtOAc (4.9 L), and stirred for about 0.5 h.
  • the mixture was filtered through celite, which was washed with EtOAc (1 L).
  • the combined filtrate was concentrated at at pressure of about 10 torr at about 75 °C.
  • Water (4.9 L) was added to the residue and the mixture was stirred for about 0.5 h.
  • the precipitate was filtered, washed with water (1 L) and dried under vacuum at about 60 °C.
  • the precipitate was stirred for about 0.5 h with MTBE (4.9 L) and filtered. This process was repeated twice more, after which the filter cake was washed with MTBE (0.5 L) and dried under vacuum at about 60 °C to provide the title compound C11.
  • Step 4 Synthesis of methyl 5-(((2,2-dimethyl-4,6-dioxo-1,3-dioxan-5-ylidene)methyl)amino)-2-isopropoxybenzoate (C21).
  • reaction mixture was then poured into a mixture of saturated aqueous NH 4 Cl solution and EtOAc with vigorous stirring.
  • EtOAc was separated, washed with water, brine, dried over Na 2 SO 4 , filtered and concentrated.
  • the residue may be used directly for subsequent work, or it may be purified by chromatography or HPLC.
  • a solution of a reactant B such as (5S)-5-(hydroxymethyl)-3-methoxypyrrolidin-2-one ( L25 ) (264 mg, 2 mmol) in 15 mL of DCM was treated with p-toluenesulfonyl chloride (760 mg, 4 mmol) and DMAP (512 mg, 4 mmol).
  • the reaction mixture was stirred for about 12 h at about 25 °C.
  • the mixture was washed with water (15mL).
  • the DCM was dried over Na 2 SO 4 , filtered and concentrated.
  • the residue was purified by silica gel chromatography to give 312 mg (52%) of the intermediate p-toluenesulfonate ester of L25.
  • the aqueous phase was back-extracted with EtOAc (10 mL), and the combined EtOAc extracts were washed with saturated aqueous sodium thiosulfate (15 mL), brine (15 mL), dried over Na 2 SO 4 , filtered and concentrated. The residue may be used directly for subsequent work, or it may be purified by chromatography or HPLC.

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PL19157789T PL3536685T3 (pl) 2014-04-04 2015-03-26 Bicykliczne skondensowane związki heteroarylowe lub arylowe i ich zastosowanie jako inhibitory IRAK4
SI201531825T SI3536685T1 (sl) 2014-04-04 2015-03-26 Biciklične kondenzirane heteroarilne ali arilne sestavine in njihova uporaba kot zaviralci IRAK-4
RS20220257A RS63024B1 (sr) 2014-04-04 2015-03-26 Kondenzovana biciklična heteroaril ili aril jedinjenja i njihova upotreba kao irak4 inhibitora
HRP20220362TT HRP20220362T1 (hr) 2014-04-04 2015-03-26 Biciklički kondenzirani heteroarilni ili arilni spojevi i njihova upotreba kao inhibitori irak4

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